Diastereoselective Synthesis of a Simplified Core of Rishirilide B.

Synlett

Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, CA 93106-9510, USA, Fax +1(805)6375651; E-mail:

Published: October 2006

A route enabling the synthesis of the stereo-triad of rishirilide B (1) from 2-hydroxy-3-methylnaphthalene-1,4-dione, is reported. Key transformations include the regioselective 1,2-Grignard addition to a tautomeric mixture of o- and p-quinones, regioselective carbamoylation of a tautomeric mixture, and a synopsis of the methods explored to convert various terminal vinyl ethers into the corresponding carboxylic acid by cleavage.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2564814PMC
http://dx.doi.org/10.1055/s-2006-950188DOI Listing

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